Production Method 1

126-30-7

100-48-1

868944-72-3

Reaction Conditions

1.1 Reagents: Triisopropyl borate ,  Piperidine, 2,2,6,6-tetramethyl-, lithium salt (1:1) ;  2 min, -78 °C; 5 min, -78 °C
1.2 Solvents: Tetrahydrofuran ;  5 min, -78 °C; overnight, 0 °C → rt
1.3 Reagents: Acetic acid
1.4 1 h, rt
1.5 Reagents: Monopotassium phosphate Solvents: Water

Reference

Synthesis of azaphenanthridines via anionic ring closure

Hansen, Henriette M.; et al, Tetrahedron, 2005, 61(42), 9955-9960

3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine-4-carbonitrile Raw materials

• 2,2-Dimethyl-1,3-propanediol
• 4-Cyanopyridine

3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine-4-carbonitrile Preparation Products

• 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine-4-carbonitrile (868944-72-3)

• 1. An arsenic trioxide nanoparticle prodrug (ATONP) potentiates a therapeutic effect on an aggressive hepatocellular carcinoma model via enhancement of intratumoral arsenic accumulation and disturbance of the tumor microenvironment?
  Xin Fu,Qing-rong Liang,Rong-guang Luo,Yan-shu Li,Xiao-ping Xiao,Lu-lu Yu,Wen-zhe Shan,Guang-qin Fan J. Mater. Chem. B, 2019,7, 3088-3099
• 2. An atomistic mechanism for the degradation of perovskite solar cells by trapped charge?
  Eunhak Lim,Jiyoung Heo,Seong Keun Kim Nanoscale, 2019,11, 11369-11378
• 3. Achieving molecular stability of racemic 4-O-benzyl-myo-inositol-1,3,5-orthoformate through crystal formation?
  Richa Sardessai,Shobhana Krishnaswamy,Mysore S. Shashidhar CrystEngComm, 2012,14, 8010-8016
• 4. Ambient electrochemical NH3 synthesis from N2 and water enabled by ZrO2 nanoparticles?
  Tong Xu,Dongwei Ma,Chengbo Li,Qian Liu,Siyu Lu,Abdullah M. Asiri,Chun Yang,Xuping Sun Chem. Commun., 2020,56, 3673-3676
• 5. An inter-tangled network of redox-active and conducting polymers as a cathode for ultrafast rechargeable batteries
  Jieun Kim,Han-Saem Park,Tae-Hee Kim,Sung Yeol Kim,Hyun-Kon Song Phys. Chem. Chem. Phys., 2014,16, 5295-5300

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridines and derivatives
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives

Comprehensive Overview of 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine-4-carbonitrile (CAS No. 868944-72-3)

3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine-4-carbonitrile (CAS No. 868944-72-3) is a boron-containing heterocyclic compound that has garnered significant attention in pharmaceutical and materials science research. This compound, often referred to as a boronic ester derivative, is characterized by its unique molecular structure, which combines a pyridine ring with a dioxaborinane moiety. Its CAS number 868944-72-3 serves as a critical identifier for researchers and regulatory bodies, ensuring precise communication in scientific literature and commercial transactions.

The growing interest in boron-based compounds like 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine-4-carbonitrile stems from their versatility in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern organic synthesis. Researchers frequently search for "boronic ester applications" or "pyridine-carbonitrile derivatives" to explore their potential in drug discovery, agrochemicals, and advanced materials. This compound's nitrile functional group further enhances its reactivity, making it a valuable intermediate in the synthesis of complex molecules.

In the context of drug development, CAS 868944-72-3 is often investigated for its role in creating kinase inhibitors and other bioactive molecules. The integration of boron atoms into pharmaceutical scaffolds has become a hot topic, particularly with the rise of proteolysis-targeting chimeras (PROTACs) and covalent inhibitors. Users searching for "boron in medicinal chemistry" or "heterocyclic building blocks" will find this compound highly relevant to their inquiries.

From a materials science perspective, 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine-4-carbonitrile offers intriguing possibilities for designing organic electronic materials. Its conjugated system and boron coordination properties make it a candidate for OLEDs and sensors. Queries like "boron-doped organic semiconductors" or "pyridine-based materials" align closely with this compound's potential applications.

The synthesis and handling of 868944-72-3 require expertise in air-sensitive chemistry, as boronic esters are prone to hydrolysis. This aspect is frequently addressed in searches for "stabilizing boronic esters" or "handling moisture-sensitive reagents." Proper storage under inert atmosphere and the use of anhydrous solvents are essential to maintain the compound's integrity.

In summary, 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine-4-carbonitrile (CAS No. 868944-72-3) represents a multifaceted tool for researchers exploring boron chemistry, pharmaceutical intermediates, and advanced materials. Its combination of a pyridine core, nitrile group, and dioxaborinane ring offers a unique platform for innovation across multiple scientific disciplines.

• 845885-86-1(3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine)
• 2710291-47-5(4-(methyl-d3)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine)
• 868944-75-6(3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)picolinonitrile)
• 878194-91-3(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isonicotinonitrile)
• 2009346-30-7(4-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbonitrile)
• 148547-17-5(Boronic acid, (4-methyl-3-pyridinyl)-, dimethyl ester)
• 868944-73-4(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)nicotinonitrile)
• 2710291-48-6(4-(methyl-d3)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,5,6-d3)
• 1171891-31-8(4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)